I have written quite a bit here about Sideways, a rare film that somehow combines wine, humor and middle age crisis into an Academy Award winning package. But until recently I had no idea how close Sideways came from never being made. In a series of posts by author Rex Pickett over at the Stage 32 blog he recounts the twists, turns and luck required to get his book published and the film made. Five parts have been posted so far with the final post coming this Thursday.

This is really not a wine story but one of perseverance and the inner workings of Hollywood. But I find the story absolutely fascinating. It also appears this story might be told in a documentary film; I have embedded the spec trailer below. If you are a fan of Sideways, I suggest you check this series out.

My friends at Grape Radio have posted a great interview with Rex Pickett, the author of ‘Sideways’ and its sequel ‘Vertical.’ Although the guys spend much of the podcast talking about ‘Sideways’ Pickett does work in plenty of details about his latest novel. Between this and the written interview posted recently by Blake Gray, I think we have covered this subject from all angles. And crossed off an item on my podcast things to do list. Actually, I would like to talk with Pickett about that new TV project he’s developing for HBO…

Since I posted my review of Rex Pickett’s new book ‘Vertical’ I’ve received email asking for more details about the author. While I hope to be able to interview Mr.Pickett on the podcast, Blake Gray has posted a no-holds barred interview with him at Palate Press.

The fascinating discussion sheds the most light I’ve yet seen on the authors’ background, motivation to write ‘Sideways’ and what his life has been like since the movie. Such transparency and gravitas makes it a must read.

It’s been almost seven years since Rex Pickett’s novel ‘Sideways’ was published in tandem with the wildly successful Alexander Payne film that made Pinot Noir a hot commodity nearly overnight. That previous novel was a treatment for a screenplay but worked well on it’s own expanding the ‘Sideways’ back story. In my review of that book, read after viewing the movie, I was enthusiastic but, unlike most other reviewers at the time, mention the elephant in the room; both main characters have a serious drinking problem. Looking back now I can see why others failed to bring up this point as ‘Sideways’ is an exaggerated and hilarious “lost weekend” road story. Pickett’s sequel ‘Vertical‘ continues this narrative but aims higher than it’s predecessor.

Let me just get this out at the beginning; if you liked ‘Sideways’ you will like ‘Vertical.’ That said, I think the sequel has quite a bit more depth and goes for a kind of redemption not seen in the dark comedy of ‘Sideways’. Told in the first-person by Miles, I was happy to read this on my eReader so I could look up some of the arcane vocabulary sprinkled in the dialogue. It’s so thick at times you can almost picture the author consulting his thesaurus to look up a seldom used synonym.

The story picks up 7 years later where the main characters, Miles and Jack, have literally changed places in their personal and professional lives. Miles has written a wildly successful book, ‘Shameless’, based loosely on the events chronicled in ‘Sideways.’ The book is immediately adapted into a hit movie and Pinot Noir sales take off. In short order, Miles has all the free Pinot he can drink, which is saying a lot since he routinely polishes off a bottle before lunch. On the other hand, Jack has lost just about everything. Now divorced with a small child he barely sees, Jack is wallowing in self-pity much the same way Miles was in the previous book. In the intervening years Miles’ mother Phillis has suffered a stroke which forces Miles to put her into an assisted living facility against her wishes. With all his success, however, Miles is still somewhat depressed but now has a ribbon of self confidence not seen earlier.

After reintroducing the characters and a graphic sex scene involving Miles and 2 female sommeliers, the narrative returns to the road with Miles and Jack driving to the International Pinot Noir Celebration (IPNC) in Willamette Valley. This extended excursion is necessitated by Phillis wanting to live with her sister in Sheboygan, Wisconsin. Miles hires Jack to help drive and a Filipino nurse, Joy, to care for his wheelchair bound mother.

Like in ‘Sideways’ Miles and Jack find very little pretense to start their drinking, even as they drive. Passing through Santa Ynez they stop at their old haunts including the now overflowing Hitching Post where Miles is treated like a rock star. At every stop in the valley all wine and food is comped as vintners thank him for their sales windfall in the wake of ‘Shameless.’ Even with an invalid mother in tow, Miles and Jack find plenty of women along the way to satisfy their lust including 2 young Spanish women on a ‘Shameless Tour’ of the area. Once Miles’ identity is revealed both are more than willing participants in a weekend fling up in Paso Robles.

This is the point in ‘Vertical’ where things start to get a bit more serious as Miles falls deeply in love with his Spanish companion. The reader gets a sense that he is questioning his life now deep into middle age. Jack, on the other hand, is living in the moment. Now flush with Miles’ cash, he takes full advantage.

There is a lot of drinking in the first three-quarters of ‘Vertical’ and after reading and seeing the events of the previous novel (and movie) the reader can only conclude the main protagonists have a serious problem with alcohol. But the new book is as funny and profane as the last one with Pickett dreaming up a hilarious set-piece after Jack consumes too much Viagra (bringing far too much meaning to, “If your erection lasts for more than 3 hours, consult your physician”). Its these comic moments that propel the reader further in the story even if more and more Pinot is consumed starting literally from when Miles and Jack get up in the morning.

‘Vertical’ is a darker book than ‘Sideways’ which I consider a black comedy. As funny as Miles drinking a spit bucket on command or being dunked in a vat of Charles Shaw Merlot is, there are other tragedies along their journey that don’t play for laughs. The final portion of the book follow the mother-son relationship between Phillis and Miles as they deadhead across the prairie to Wisconsin. This gives ‘Vertical’ a satisfying conclusion and a gravitas missing from ‘Sideways.’ And as the story comes to it’s end, there is clearly plenty of room for a third book to be written but if the tale stops here the reader will be satisfied.

Rex Pickett is to be commended for producing a thoughtful sequel and not just churning out something to cash in on his success. ‘Vertical’ seems more autobiographical than ‘Sideways’ as the author certainly had many of the same opportunities depicted in this book. Along the way plenty of Oregon Pinot Noir is consumed with vivid tasting notes that will certainly benefit those mentioned but I doubt there will be another surge in Pinot sales. It’s unclear if ‘Vertical’ will be made into a movie but seems likely since the story here is as cinematic as the first. We can only hope that the original cast is enticed back to bring these characters back to life.

I enthusiastically recommend ‘Vertical‘ but will caution readers who are easily offended by graphic sex scenes and salty ‘guy talk’ there is plenty of both in this novel. But if you do venture down the road with Miles and Jack you are likely to be satisfied and perhaps touched by the journey.

I’m about two-thirds of my way though Rex Pickett’s sequel to Sideways called Vertical (yes, a review is forthcoming). While the book is an apt successor to it’s wildly successful predecessor, I don’t think we will see as much of an impact on the wine industry, or Pinot Noir in particular, this time even if they manage to make a movie from it (original cast, please).

But I do think we might see a Sideways-style effect if Pickett’s TV project, “The Nose,” is ever produced. Loosely based on wine critic Robert Parker and podcaster and all around hustler Gary Vaynerchuk, the series is being developed for HBO. As Blake Gray points out in his post there is a long road ahead before this gets a green light but at least the concept sounds like it might work. My opinion is not shared by Blake’s commenters right now but I think they are wrong 😉

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Tim Elliott is a marketer, blogger and podcaster based in the Twin Cities. He founded Winecast in 2004 to share his passion for wine online. Tim has also written for Minneapolis City Pages, Vineyard & Winery Management Magazine and Honest Cooking.